It is known that 1-chloro-3,3,3-trifluoropropene is an environment-adaptive material that is not categorized as an ozone depleting substance and is suitably usable as a solvent, a cleaning agent, a coolant, a refrigerant, a working fluid, a propellant, a raw material for fluorinated resins etc. Herein, 1-chloro-3,3,3-trifluoropropene exists as trans and cis geometric isomers. The trans and cis isomers of 1-chloro-3,3,3-trifluoropropene are hereinafter sometimes called “1233E” and “1233Z”, respectively, by their identification numbers with additional symbols. The 1-chloro-3,3,3-trifluoropropene is simply called “1233” in the case where there is no need to distinguish the trans and cis isomers or in the case where it refers to a mixture of the trans and cis isomers. Further, there is known 1,3,3,3-tetrafluoropropene as a material relevant to 1-chloro-3,3,3-trifluoropropene. Trans and cis isomers of 1,3,3,3-tetrafluoropropene are hereinafter sometimes called “1234E” and “1234Z”, respectively. The 1,3,3,3-tetrafluoropropene is simply called “1234” in the case where there is no need to distinguish the trans and cis isomers or in the case where it refers to a mixture of the trans and cis isomers.
As a production method of 1233, Patent Document 1 discloses a process of synthesizing 1233 by reaction of 1,1,1,3,3-pentafluoropropane (sometimes called “245fa”) and hydrogen chloride in gas phase in the presence of a solid catalyst.
As a production method of 1234, Patent Document 2 discloses a process of synthesizing 1234 by fluorination of 1,1,1,3,3-pentachloropropane (sometimes called “240fa”) with hydrogen fluoride in liquid phase in the presence of an antimony catalyst.
There is however a problem that hydrogen chloride containing hydrogen fluoride is generated during the synthesis of the 245fa by the fluorination of the 240fa. As the hydrogen chloride containing hydrogen fluoride is more difficult to use than pure hydrogen chloride with no hydrogen fluoride, it is often the case that the hydrogen chloride containing hydrogen fluoride is disposed of as a waste after neutralization treatment.
Further, saturated hydrochlorofluorocarbons (sometimes called “HCFC”) such as 3-chloro-1,1,1,3-tetrafluoropropane (sometimes called “244fa”) and 3,3,-dichloro-1,1,1-trifluoropropane (sometimes called “243fa”) may be generated as impurities during the synthesis of the 245fa by the fluorination of the 240fa as discussed in Examples of Patent Document 2.
Patent Document 3 discloses a plasma decomposition apparatus for decomposition of HCFC. Patent Document 4 discloses, as an easy combustion method of HCFC, a process of decomposing an organic or inorganic halide in the coexistence of an alkali metal compound in combustion frame. However, for example, the complete combustion of 3-chloro-1,1,1,3-tetrafluoropropane (244fa) theoretically requires 2 mol of hydrogen per 1 mol of the 244fa and gives 6 mol of earth-warming carbon dioxide gas (see the following scheme). Although it is common practice to produce the hydrogen required for such complete combustion by a steam reforming process, the steam reforming process causes emission of carbon dioxide. It is thus hardly said that the combustion of the HCFC is an environmentally suitable treatment process.2CF3CH2CHClF+4H2+7O2→6CO2+2H2O+8HF+2HClAs compared to the saturated HCFC compound, 1-chloro-3,3,3-trifluoropropene (1233) has a double bond in the molecule and can be easily decomposed because of its high rate of reaction with OH radicals in the air. Accordingly, the 1233 is an environment-adaptive chlorofluorocarbon that has less influence on the ozone layer. Patent Document 5 discloses a blowing agent containing 1233 as the 1233 shows good heat insulating properties.
Patent document 6 discloses a process of producing 1233 by dehydrofluorination of 3-chloro-1,1,1,3-tetrafluoropropane (244fa) in the presence of a catalyst under the conditions sufficient for dehydrofluorination reaction. However, there occurs dehydrochlorination in parallel with the dehydrofluorination so that 1,1,1,3-tetrafluoropropene (1234) is also generated (as a by-product) in the production process. The selectivity of the 1233 is lowered due to the by-production of the 1234.